Dextromethorphan (hydrobromide hydrate)
(Synonyms: 氢溴酸右美沙芬) 目录号 : GC43428
Dextromethorphan (hydrobromide hydrate)是一种与可待因类似的levorphanol的D型异构体。Dextromethorphan不像其他几种吗啡衍生物那样引起阿片类活性。
Cas No.:6700-34-1
Sample solution is provided at 25 µL, 10mM.
Dextromethorphan (hydrobromide hydrate) is a D-isomer of levorphanol, similar to codeine. Unlike several other morphine derivatives, Dextromethorphan does not cause opioid activity [1]. Dextromethorphan is a conformational antagonist and voltage-dependent antagonist of N-methyl D-aspartate (NMDA) control ion channels [2]. Due to its strong antitussive effect, Dextromethorphan is widely used as a cough suppressant. Dextromethorphan has been used in multimodal analgesic treatment for acute and neuropathic pain [3-4].
In vitro, Dextromethorphan (12.5, 25, 50 and 100μM; 18h) dose-dependently inhibited the expression of co-stimulatory molecules (CD80, CD86 and CD40) in LPS-induced mouse bone marrow-derived dendritic cells (BMDCs), and reduced the production of reactive oxygen species, pro-inflammatory cytokines and chemokines in the cells [5]. Under an intracellular/extracellular pH gradient of 5.5/7.3, Dextromethorphan (0-100μM; 10min) reversibly inhibited the voltage-gated proton current in BV2 microglial cells, with an IC50 of 51.7μM [6].
In vivo, Dextromethorphan (1 and 3mg/ml; 8 weeks; orally in drinking water) long-term treatment significantly improved the plasma insulin concentration, glucose tolerance and islet cell quality of 2-type diabetic (T2DM) mice [7]. Dextromethorphan (32mg/kg/day; single-dose; i.p.) pretreatment for 30min produced a similar antidepressant effect in C57BL/6 mice in the tail suspension test (TST), but failed to produce a similar antidepressant effect 24 hours after administration [8].
References:
[1] Mayet S. Atypical opioids[J]. Southern African Journal of Anaesthesia and Analgesia, 2023: 147-152.
[2] Werling L L, Lauterbach E C, Calef U. Dextromethorphan as a potential neuroprotective agent with unique mechanisms of action[J]. The neurologist, 2007, 13(5): 272-293.
[3] Bolser, D.C., Aziz, S.M., DeGennaro, F.C., et al. Antitussive effects of GABAB agonists in the cat and guinea-pig. Br. J. Pharmacol. 110(1), 491-495 (1993).
[4] Chen, Y.W., Chu, K.S., Lin, C.N., et al. Dextromethorphan or dextrorphan have a local anesthetic effect on infiltrative cutaneous analgesia in rats. Anesth. Analg. 104(5), 1251-1255 (2007).
[5] Chen D Y, Song P S, Hong J S, et al. Dextromethorphan inhibits activations and functions in dendritic cells[J]. Journal of Immunology Research, 2013, 2013(1): 125643.
[6] Song JH, Yeh JZ. Dextromethorphan inhibition of voltage-gated proton currents in BV2 microglial cells. Neurosci Lett. 2012;516(1):94-98.
[7] Marquard J, Otter S, Welters A, et al. Characterization of pancreatic NMDA receptors as possible drug targets for diabetes treatment[J]. Nature medicine, 2015, 21(4): 363-372.
[8] Saavedra JS, Garrett PI, Honeycutt SC, Peterson AM, White JW, Hillhouse TM. Assessment of the rapid and sustained antidepressant-like effects of dextromethorphan in mice. Pharmacol Biochem Behav. 2020;197:173003.
Dextromethorphan (hydrobromide hydrate)是一种与可待因类似的levorphanol的D型异构体。Dextromethorphan不像其他几种吗啡衍生物那样引起阿片类活性 [1]。Dextromethorphan是N-甲基 D-天冬氨酸（NMDA）控制离子通道的变构拮抗剂和电压依赖性通道的拮抗剂 [2]。由于其强烈的止咳作用，Dextromethorphan被广泛用作咳嗽抑制剂。Dextromethorphan已用于急性和神经性疼痛的多模态镇痛治疗[3-4]。
在体外，Dextromethorphan（12.5, 25, 50和100μM; 18h）处理剂量依赖性地抑制了LPS诱导的小鼠骨髓源性树突状细胞（BMDCs）中共刺激分子（CD80、CD86和CD40）的表达，减少了细胞中活性氧、促炎细胞因子和趋化因子的产生 [5]。在细胞内/细胞外pH梯度为5.5/7.3的情况下，Dextromethorphan(0-100μM; 10min)可逆地抑制小胶质细胞BV2细胞中电压门控质子电流，IC50为51.7μM [6]。
在体内，Dextromethorphan（1和3mg/ml; 8 weeks; drinking water orally）长期治疗显著改善了2型糖尿病（T2DM）小鼠的血浆胰岛素浓度和葡萄糖耐量和胰岛细胞质量 [7]。Dextromethorphan（32mg/kg/day; single-dose; i.p.）预处理30min对尾部悬浮试验（TST）中的C57BL/6小鼠产生类似抗抑郁作用，但在给药24小时后未能产生类似抗抑郁作用 [8]。
| Cell experiment [1]: | |
Cell lines | BMDC cells |
Preparation Method | The expression of cell surface molecules was quantified by flow cytometry as follows. The Dextromethorphan was prepared in PBS as a 12.5 millimolar stock solution. Aliquots of 2 × 105 immature BMDCs or MDDCs were cultured in the presence or absence of Dextromethorphan for 1h and then stimulated with 100ng/mL Escherichia coli serotype O26:B6 LPS or 100ng/mL LPS plus 10ng/mL IFN-γ for 18h. The control group was treated with PBS alone. After incubation, DCs were harvested and stained with the following antibodies for 45min on ice (1μg/mL diluted in PBS/1.0% FCS (v/v)): FITC-conjugated anti-human CD1a+ or anti-murine CD11c+; phycoerythrin (PE)-conjugated anti-human CD80+, anti-human CD83+, anti-murine CD40, anti-murine CD80, anti-murine CD86, anti-murine MHC class I, anti-murine MHC class II or isotype-matched control mAbs; or PE-conjugated anti-human HLA-DR. After washing with PBS, the cells were analyzed in a FACSCalibur flow cytometer, and the data were analyzed using WINMDI software. |
Reaction Conditions | 12.5, 25, 50 and 100μM; 18h |
Applications | The dextromethorphan treatment dose-dependently inhibited the expression of co-stimulatory molecules (CD80, CD86 and CD40) in mouse bone marrow-derived dendritic cells (BMDCs) induced by LPS. |
| Animal experiment [2]: | |
Animal models | C57BL/6 mice |
Preparation Method | Dextromethorphan, Imipramine hydrochloride and Quinidine sulfate (QND) were dissolved in 0.9% saline and administered via intraperitoneal (i.p.) injection at a volume of 10ml/kg. Drug doses and pretreatment times were selected based on published literature and are as follows: Dextromethorphan (32mg/kg; 30min or 24h), imipramine (0 or 20mg/kg; 30min), and QND (0 or 32mg/kg; 30min). To assess the sustained antidepressant-like effects of Dextromethorphan, a 24h pretreatment time was used prior to the tail suspension test (TST). |
Dosage form | 32mg/kg/day; single-dose; i.p. |
Applications | Dextromethorphan pretreatment for 30 minutes produced an acute antidepressant-like effect in the tail suspension test (TST) in C57BL/6 mice, but no such effect was observed 24 hours after administration. |
References: | |
| Cas No. | 6700-34-1 | SDF | |
| 别名 | 氢溴酸右美沙芬 | ||
| Canonical SMILES | CN1[C@@H]2[C@@]3([H])CCCC[C@@]3(CC1)C4=CC(OC)=CC=C4C2 | ||
| 分子式 | C18H25NO•HBr [H2O] | 分子量 | 370.3 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 12 mg/ml,Ethanol: 20 mg/ml,PBS (pH 7.2): 5 mg/ml | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.7005 mL | 13.5026 mL | 27.0051 mL |
| 5 mM | 0.5401 mL | 2.7005 mL | 5.401 mL |
| 10 mM | 0.2701 mL | 1.3503 mL | 2.7005 mL |
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动物平均体重 | g | |
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动物数量 | 只 |
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